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1,2-Dichloroethane → 2-({[4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetyl}amino)-2-[3-(trifluoromethyl)phenyl]ethyl carbamate

HRID 220713
Notes
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Reaction equation

HRID 220713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:18][CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[C:10](=[O:17])[N:11]([CH2:13][C:14](O)=[O:15])[CH:12]=2)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:39](=[O:53])([O:41][CH2:42][CH:43]([NH2:52])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46](Cl)[C:45]=1Cl)[NH2:40].Cl>CN(C=O)C>[C:39](=[O:53])([O:41][CH2:42][CH:43]([NH:52][C:14](=[O:15])[CH2:13][N:11]1[CH:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]([CH2:18][CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[C:10]1=[O:17])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([C:20]([F:23])([F:22])[F:21])[CH:45]=1)[NH2:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 59536810[4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetic acidHCID 595368632-Amino-2-(2,3-dichlorophenyl)ethyl carbamate

Product 1

HCID 59536776
2-({[4-(4-Chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetyl}amino)-2-[3-(trifluoromethyl)phenyl]ethyl carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A quantity of 58 mg (0.11 mmol) of [4-(4-chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]acetic acid from Example 184A was dissolved in 2 ml of DMF, and the solution was admixed with 28 mg (0.15 mmol) of EDC and with 20 mg (0.15 mmol) of HOBt and subsequently stirred at room temperature for 20 minutes. Then 42 mg (0.12 mmol) of the compound from Example 183A were added and the mixture was left with stirring at room temperature for 16 h. For work-up, 100 μl of 1N hydrochloric acid were added and the crude product was purified directly by preparative HPLC [Method 19]. This gave 13 mg (18% of theory) of the target compound.

Workup

  1. waitthe mixture was left
  2. stirringwith stirring at room temperature for 16 h
  3. customthe crude product was purified directly by preparative HPLC [Method 19]

Sources & evidence

ORD record
ord-1110d95484424968b2dd561a8fc26bc8
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202895B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes